ZA200603338B - Method for producing (3-oxo-2,3-dihydro-1H-isoindol-1yl) acetylguanidine derivatives - Google Patents
Method for producing (3-oxo-2,3-dihydro-1H-isoindol-1yl) acetylguanidine derivatives Download PDFInfo
- Publication number
- ZA200603338B ZA200603338B ZA200603338A ZA200603338A ZA200603338B ZA 200603338 B ZA200603338 B ZA 200603338B ZA 200603338 A ZA200603338 A ZA 200603338A ZA 200603338 A ZA200603338 A ZA 200603338A ZA 200603338 B ZA200603338 B ZA 200603338B
- Authority
- ZA
- South Africa
- Prior art keywords
- formula
- carbon atoms
- compound
- trifluoromethyl
- alkyl
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title claims description 10
- HLFLSXJZAJUCFK-UHFFFAOYSA-N n-carbamimidoyl-n-(3-oxo-1,2-dihydroisoindol-1-yl)acetamide Chemical class C1=CC=C2C(N(C(=O)C)C(N)=N)NC(=O)C2=C1 HLFLSXJZAJUCFK-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 92
- 125000004432 carbon atom Chemical group C* 0.000 claims description 57
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 50
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 36
- 150000003839 salts Chemical class 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 27
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 150000001408 amides Chemical class 0.000 claims description 18
- XTBAPWCYTNCZTO-UHFFFAOYSA-N isoindol-1-one Chemical class C1=CC=C2C(=O)N=CC2=C1 XTBAPWCYTNCZTO-UHFFFAOYSA-N 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- -1 trifluoromethoxy, 2,2,2-trifluoroethoxy Chemical group 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 150000002148 esters Chemical class 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 11
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 10
- 239000012954 diazonium Substances 0.000 claims description 8
- 150000001989 diazonium salts Chemical class 0.000 claims description 7
- 238000007363 ring formation reaction Methods 0.000 claims description 6
- 150000001851 cinnamic acid derivatives Chemical class 0.000 claims description 5
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 4
- 125000005250 alkyl acrylate group Chemical group 0.000 claims description 4
- 238000002425 crystallisation Methods 0.000 claims description 4
- 230000008025 crystallization Effects 0.000 claims description 4
- XUYJLQHKOGNDPB-UHFFFAOYSA-N phosphonoacetic acid Chemical compound OC(=O)CP(O)(O)=O XUYJLQHKOGNDPB-UHFFFAOYSA-N 0.000 claims description 4
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 3
- 230000004913 activation Effects 0.000 claims description 3
- 150000002828 nitro derivatives Chemical class 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 238000005580 one pot reaction Methods 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 12
- 208000035475 disorder Diseases 0.000 claims 11
- 239000003814 drug Substances 0.000 claims 10
- 238000011282 treatment Methods 0.000 claims 8
- 238000011321 prophylaxis Methods 0.000 claims 7
- 230000003176 fibrotic effect Effects 0.000 claims 5
- 239000000654 additive Substances 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 210000003169 central nervous system Anatomy 0.000 claims 4
- 230000000302 ischemic effect Effects 0.000 claims 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims 4
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 3
- 239000004480 active ingredient Substances 0.000 claims 3
- 210000000056 organ Anatomy 0.000 claims 3
- 210000001519 tissue Anatomy 0.000 claims 3
- 206010019280 Heart failures Diseases 0.000 claims 2
- 230000002093 peripheral effect Effects 0.000 claims 2
- 230000000144 pharmacologic effect Effects 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 210000002307 prostate Anatomy 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 2
- 206010002383 Angina Pectoris Diseases 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 101100515517 Arabidopsis thaliana XI-I gene Proteins 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 1
- 208000003495 Coccidiosis Diseases 0.000 claims 1
- 206010010904 Convulsion Diseases 0.000 claims 1
- 208000020401 Depressive disease Diseases 0.000 claims 1
- 206010048554 Endothelial dysfunction Diseases 0.000 claims 1
- 208000007530 Essential hypertension Diseases 0.000 claims 1
- 208000010496 Heart Arrest Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 206010020850 Hyperthyroidism Diseases 0.000 claims 1
- 206010020880 Hypertrophy Diseases 0.000 claims 1
- 206010023076 Isosporiasis Diseases 0.000 claims 1
- 206010027476 Metastases Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000028017 Psychotic disease Diseases 0.000 claims 1
- 208000007536 Thrombosis Diseases 0.000 claims 1
- 230000009692 acute damage Effects 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 230000032683 aging Effects 0.000 claims 1
- 206010003119 arrhythmia Diseases 0.000 claims 1
- 230000006793 arrhythmia Effects 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 230000000747 cardiac effect Effects 0.000 claims 1
- 230000001451 cardiotoxic effect Effects 0.000 claims 1
- 230000004663 cell proliferation Effects 0.000 claims 1
- 230000009693 chronic damage Effects 0.000 claims 1
- 208000037976 chronic inflammation Diseases 0.000 claims 1
- 208000037893 chronic inflammatory disorder Diseases 0.000 claims 1
- 230000036461 convulsion Effects 0.000 claims 1
- 230000006378 damage Effects 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 230000008694 endothelial dysfunction Effects 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-M fumarate(1-) Chemical compound OC(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-M 0.000 claims 1
- 206010020718 hyperplasia Diseases 0.000 claims 1
- 210000003734 kidney Anatomy 0.000 claims 1
- 230000037356 lipid metabolism Effects 0.000 claims 1
- 210000004185 liver Anatomy 0.000 claims 1
- 201000004792 malaria Diseases 0.000 claims 1
- 230000009401 metastasis Effects 0.000 claims 1
- 208000010125 myocardial infarction Diseases 0.000 claims 1
- 210000001428 peripheral nervous system Anatomy 0.000 claims 1
- 244000144977 poultry Species 0.000 claims 1
- 230000010410 reperfusion Effects 0.000 claims 1
- 230000035939 shock Effects 0.000 claims 1
- 238000001356 surgical procedure Methods 0.000 claims 1
- 208000005057 thyrotoxicosis Diseases 0.000 claims 1
- 238000002054 transplantation Methods 0.000 claims 1
- 208000003663 ventricular fibrillation Diseases 0.000 claims 1
- 210000001835 viscera Anatomy 0.000 claims 1
- 239000002904 solvent Substances 0.000 description 18
- 229960004198 guanidine Drugs 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- 239000002585 base Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 150000002431 hydrogen Chemical group 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
- 238000009835 boiling Methods 0.000 description 11
- 239000012442 inert solvent Substances 0.000 description 9
- 239000004215 Carbon black (E152) Substances 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 229930195733 hydrocarbon Natural products 0.000 description 7
- 150000002430 hydrocarbons Chemical class 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 150000008282 halocarbons Chemical class 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 4
- 238000010626 work up procedure Methods 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- MGRUNSIBUNAFKA-UHFFFAOYSA-N n-(diaminomethylidene)-2-(3-oxo-1,2-dihydroisoindol-1-yl)acetamide Chemical class C1=CC=C2C(CC(=O)NC(=N)N)NC(=O)C2=C1 MGRUNSIBUNAFKA-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- 206010013786 Dry skin Diseases 0.000 description 2
- 229910004039 HBF4 Inorganic materials 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 238000010640 amide synthesis reaction Methods 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000013375 chromatographic separation Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 description 1
- SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 1
- KAUMDYDNLPQESC-UHFFFAOYSA-N 3-hydroxy-2,3-dihydroisoindol-1-one Chemical class C1=CC=C2C(O)NC(=O)C2=C1 KAUMDYDNLPQESC-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 101000939500 Homo sapiens UBX domain-containing protein 11 Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical class ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 108091006647 SLC9A1 Proteins 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 102100030980 Sodium/hydrogen exchanger 1 Human genes 0.000 description 1
- 102100029645 UBX domain-containing protein 11 Human genes 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000005595 deprotonation Effects 0.000 description 1
- 238000010537 deprotonation reaction Methods 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000006170 formylation reaction Methods 0.000 description 1
- 229960000789 guanidine hydrochloride Drugs 0.000 description 1
- PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- NGGXACLSAZXJGM-UHFFFAOYSA-N n-(diaminomethylidene)acetamide Chemical class CC(=O)N=C(N)N NGGXACLSAZXJGM-UHFFFAOYSA-N 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/46—Iso-indoles; Hydrogenated iso-indoles with an oxygen atom in position 1
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P25/24—Antidepressants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
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- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
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- A61P33/06—Antimalarials
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- A—HUMAN NECESSITIES
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- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
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Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10356717A DE10356717A1 (de) | 2003-12-02 | 2003-12-02 | Verfahren zur Herstellung von (3-Oxo-2,3-dihydro-1H-isoindol-1-yl)-acetylguanidin-Derivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200603338B true ZA200603338B (en) | 2007-06-27 |
Family
ID=34638338
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200603338A ZA200603338B (en) | 2003-12-02 | 2006-04-26 | Method for producing (3-oxo-2,3-dihydro-1H-isoindol-1yl) acetylguanidine derivatives |
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| EP (1) | EP1692105B1 (de) |
| JP (1) | JP4809774B2 (de) |
| KR (1) | KR101202604B1 (de) |
| CN (1) | CN100526297C (de) |
| AR (1) | AR046733A1 (de) |
| AT (1) | ATE395334T1 (de) |
| AU (1) | AU2004295056B2 (de) |
| BR (1) | BRPI0417147A (de) |
| CA (1) | CA2548020C (de) |
| CR (1) | CR8376A (de) |
| CY (1) | CY1108187T1 (de) |
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| HR (1) | HRP20080253T3 (de) |
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| MA (1) | MA28220A1 (de) |
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| PE (1) | PE20051037A1 (de) |
| PL (1) | PL1692105T3 (de) |
| PT (1) | PT1692105E (de) |
| RS (1) | RS50571B (de) |
| RU (1) | RU2397159C2 (de) |
| SI (1) | SI1692105T1 (de) |
| TN (1) | TNSN06167A1 (de) |
| TW (1) | TWI334348B (de) |
| UA (1) | UA83883C2 (de) |
| UY (1) | UY28648A1 (de) |
| WO (1) | WO2005054195A1 (de) |
| ZA (1) | ZA200603338B (de) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200812962A (en) * | 2006-07-12 | 2008-03-16 | Astrazeneca Ab | New compounds I/418 |
| CN102007138B (zh) * | 2008-04-16 | 2014-05-21 | 橘生药品工业株式会社 | 吡唑衍生物的半富马酸盐 |
| RU2518740C1 (ru) * | 2013-03-22 | 2014-06-10 | Федеральное государственное автономное образовательное учреждение высшего профессионального образования "ЮЖНЫЙ ФЕДЕРАЛЬНЫЙ УНИВЕРСИТЕТ" | СРЕДСТВО, ИНГИБИРУЮЩЕЕ Na+/H+-ОБМЕН, И ДИГИДРОХЛОРИД 2-(3,4-МЕТИЛЕНДИОКСИФЕНИЛ)-9-МОРФОЛИНОЭТИЛИМИДАЗО[1,2-a]БЕНЗИМИДАЗОЛА |
| CN107778238B (zh) * | 2016-08-29 | 2022-07-22 | 中山大学 | 一种3，4-二氢异喹啉-1-酮的合成新方法 |
| CN107286074B (zh) * | 2017-08-16 | 2019-08-20 | 厦门华厦学院 | 3-羟基异吲哚-1-酮衍生物及其制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4946842A (en) * | 1985-07-05 | 1990-08-07 | Smith Kline & French Laboratories Limited | Novel guanidino pyridazinones as cardiac stimulants |
| DE19737224A1 (de) * | 1997-08-27 | 1999-03-18 | Hoechst Marion Roussel De Gmbh | Pharmazeutisches Kombinationspräparat aus einem Inhibitor des Natrium-Wasserstoff-Austauschers und einem Arzneimittel zur Behandlung von Herz-Kreislauferkrankungen |
| DE19832429A1 (de) * | 1998-07-18 | 2000-01-20 | Hoechst Marion Roussel De Gmbh | Imidazolderivate mit Biphenylsulfonylsubstitution, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| EP1385823B1 (de) * | 2001-04-09 | 2006-12-13 | Chiron Corporation | Guanidinoverbindungen als melanocortin-4-rezeptor (mc4-r) agonisten |
| FR2840302B1 (fr) * | 2002-06-03 | 2004-07-16 | Aventis Pharma Sa | Derives d'isoindolones, procede de preparation et intermediaire de ce procede a titre de medicaments et compositions pharmaceutiques les renfermant |
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2003
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- 2004-11-19 SI SI200430747T patent/SI1692105T1/sl unknown
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- 2004-11-19 NZ NZ547625A patent/NZ547625A/en not_active IP Right Cessation
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- 2006-06-01 EG EGNA2006000508 patent/EG25498A/xx active
- 2006-06-02 MA MA29077A patent/MA28220A1/fr unknown
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2007
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